CN104862350A - Method for preparing 1, 3-dilinolein-2-palmitic acid triglyceride - Google Patents
Method for preparing 1, 3-dilinolein-2-palmitic acid triglyceride Download PDFInfo
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- CN104862350A CN104862350A CN201510227309.9A CN201510227309A CN104862350A CN 104862350 A CN104862350 A CN 104862350A CN 201510227309 A CN201510227309 A CN 201510227309A CN 104862350 A CN104862350 A CN 104862350A
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- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000003921 oil Substances 0.000 claims abstract description 61
- 235000019198 oils Nutrition 0.000 claims abstract description 61
- 241001233037 catfish Species 0.000 claims abstract description 46
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000007787 solid Substances 0.000 claims abstract description 25
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 18
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 8
- 108090001060 Lipase Proteins 0.000 claims abstract description 5
- 102000004882 Lipase Human genes 0.000 claims abstract description 5
- 239000004367 Lipase Substances 0.000 claims abstract description 5
- 235000019421 lipase Nutrition 0.000 claims abstract description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 5
- 239000008158 vegetable oil Substances 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000199 molecular distillation Methods 0.000 claims description 8
- 108010048733 Lipozyme Proteins 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical group NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 4
- 235000019486 Sunflower oil Nutrition 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000002600 sunflower oil Substances 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000001020 rhythmical effect Effects 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 abstract description 24
- 239000002994 raw material Substances 0.000 abstract description 7
- 235000021314 Palmitic acid Nutrition 0.000 abstract description 5
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract description 2
- 235000013350 formula milk Nutrition 0.000 abstract description 2
- 235000013336 milk Nutrition 0.000 abstract description 2
- 239000008267 milk Substances 0.000 abstract description 2
- 210000004080 milk Anatomy 0.000 abstract description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 23
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 11
- 238000009826 distribution Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 6
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- 238000009834 vaporization Methods 0.000 description 4
- 230000008016 vaporization Effects 0.000 description 4
- 241001417930 Siluridae Species 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 235000020256 human milk Nutrition 0.000 description 3
- 210000004251 human milk Anatomy 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 238000005204 segregation Methods 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229940099352 cholate Drugs 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 210000001268 chyle Anatomy 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 210000002490 intestinal epithelial cell Anatomy 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 108091016642 steapsin Proteins 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C11/00—Milk substitutes, e.g. coffee whitener compositions
- A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a method for preparing 1, 3-dilinolein-2-palmitic acid triglyceride. The method includes: melting the catfish oil at the temperature of 50-60 DEGC for 30-60 min, reducing the temperature to 15-30 DEG C at the cooling rate of 1-5 DEG C/min for 5-48 h, eliminating the liquid oil through the filtering mode and obtaining the catfish oil solid lipid which is rich in palmitic acid; and taking sn-1, 3-digit specificity lipase as the catalyst and the free fatty acid which comes from high oleic acid vegetable oil as the acyl donor, conducting acidolysis on the catfish oil solid lipid, eliminating the free fatty acid and obtaining the product which is rich in 1, 3-dilinolein-2-palmitic acid triglyceride. The 1, 3-dilinolein-2-palmitic acid triglyceride is low in price of raw materials, high in content and capable of being applied to infant formula milk as the additive.
Description
Technical field
The invention belongs to grease technical field, be specifically related to the method that OPO product is rich in a kind of acidolysis preparation.
Background technology
Breast milk is the food of infant's the best, provides the nearly all nutritive substance comprised needed for infant, and wherein fat occupies about 3 ~ 5% of breast milk, but for infant provides the energy of about more than 50%.In these fat, the content of triglyceride level is more than 98%.In breast milk, the content of palmitinic acid is 20 ~ 30%, a large amount of saturated fatty acids (palmitinic acid) is in the sn-2 position of triglyceride level, and unsaturated fatty acids is at sn-1,3, it is saturated fatty acid that cause which form a large amount of sn-2, sn-1, and 3 is the triglyceride level of unsaturated fatty acids, as OPO (OPO).
Fat is after infant takes in, first nearly 10 ~ 30% can become sn-2 by tongue lipase and gastric lipase enzyme hydrolysis, 3 triglycerides, and then become sn-2 Tegin 55G and lipid acid by the effect hydrolysis of steapsin and cholate, sn-2 Tegin 55G can directly be absorbed by intestinal epithelial cell, esterification is triglyceride level, then is converted into each position that chyle breast grain is transported to health and provides energy.The absorption of lipid acid has important relationship with its saturation ratio and chain length.Calcium ions and magnesium ions in the easy consubstantiality of chain saturated fatty acids forms dystectic soap, excretes.For infant, the loss of energy can be caused like this, also may cause constipation or the consequence such as intestines are rotten simultaneously.Therefore, palmitinic acid can avoid these untoward reactions in sn-2 position.Correlative study is also reported, carry out feeding infant by the fat of the fat and stochastic distribution palmitinic acid that adopt high sn-2 palmitinic acid, palmitinic acid is more soft at the ight soil of the fatty baby of sn-2 position.Meanwhile, relevant report also shows, and adopts OPO feeding infant, and than adopting the isomers 1,2-bis-oleic acid-3-palmitic acid three ester (OOP) of OPO to feed, the transport velocity of OPO is faster.Therefore, the triglyceride level of palmitinic acid in sn-2 position of this special construction, all significant to the digestion of fat in infants, absorption and metabolism.
At present, some bibliographical informations adopt tripalmitin and lard to prepare the method for OPO product.Although palm stearin has palmitinic acid on sn-2 position, it is at sn-1, and 3 palmitinic acids also having an identical amount, therefore need to adopt larger substrate ratio to prepare OPO product.Also someone adopts palm stearin to be raw material, prepare the OPO of higher degree, but technics comparing is complicated, is difficult to obtain suitability for industrialized production with the method for alcoholysis and resterification.Therefore, find one to have higher palmitic acid content in sn-2 position, lower total palmitic acid content, general grease can be obtained again simultaneously, for exploitation OPO product, just there is very important meaning.
Summary of the invention
The object of this part is some aspects of general introduction embodiments of the invention and briefly introduces some better embodiment.May do in the specification digest and denomination of invention of this part and the application a little simplify or omit with avoid making this part, specification digest and denomination of invention object fuzzy, and this simplification or omit and can not be used for limiting the scope of the invention.
In view of above-mentioned and/or existingly prepare Problems existing in the method for OPO, propose the present invention.
Therefore, one object of the present invention be to provide a kind of economically viable be the preparation method of the OPO of raw material with catfish oil.
For solving the problems of the technologies described above, according to an aspect of the present invention, the invention provides following technical scheme: a kind of method preparing OPO, it comprises, by catfish oil 50 ~ 60 DEG C of fusings, keep 30 ~ 60min, and be cooled to 15 ~ 30 DEG C with the rate of temperature fall of 1 ~ 5 DEG C/min, after catfish oil is kept 5 ~ 48h at this temperature, adopt the mode of filtering to remove liquid oil, obtain the solid fat composition of catfish oil being rich in palmitinic acid in sn-2 position; With sn-1,3 specific lipases are catalyzer, and with the free fatty acids of high gas oil ratio vegetable oil source for acry radical donor, described in acidolysis, the solid fat composition of catfish oil, obtains the product being rich in OPO after removing free fatty acids.
As a kind of preferred version preparing the method for OPO of the present invention, wherein: described catalyzer is Lipozyme RM IM and/or Lipozyme TL IM.
As a kind of preferred version preparing the method for OPO of the present invention, wherein: described high gas oil ratio vegetables oil is one or more in high gas oil ratio rapeseed oil, high oleic sunflower oil and sweet oil.
As a kind of preferred version preparing the method for OPO of the present invention, wherein: described acidolysis, its temperature of reaction is 40 DEG C ~ 70 DEG C.
As a kind of preferred version preparing the method for OPO of the present invention, wherein: described catfish oil is 1:1 ~ 10 with the mol ratio of free fatty acids.
As preparation 1 of the present invention, a kind of preferred version of the method for 3-bis-oleic acid-2-palmitic acid three ester, wherein: described acidolysis is rhythmic reaction, its enzyme concentration is 3% ~ 15wt%, reaction times is 1h ~ 5h, and stir speed (S.S.) is 300r/min ~ 800r/min.
As a kind of preferred version preparing the method for OPO of the present invention, wherein: described acidolysis is successive reaction, its substrate residence time is at 0.5h ~ 3h.
As a kind of preferred version preparing the method for OPO of the present invention, wherein: described removing free fatty acids is centrifugation.
As preparation 1 of the present invention, a kind of preferred version of the method for 3-bis-oleic acid-2-palmitic acid three ester, wherein: described removing free fatty acids is molecular distillation, its vaporization temperature is 180 DEG C ~ 190 DEG C, rotating speed is 110 ~ 130rpm, and absolute pressure is 2 ~ 3Pa.
As a kind of preferred version preparing the method for OPO of the present invention, wherein: described removing free fatty acids is underpressure distillation.
Beneficial effect of the present invention: the present invention raw materials used catfish oil is cheap, wide material sources, simultaneously because catfish oil self contains higher sn-2 palmitinic acid and lower total palmitic acid content, in acidolysis reaction, free fatty acids ratio used is little, thus has larger market outlook.
Embodiment
For enabling above-mentioned purpose of the present invention, feature and advantage become apparent more, are described in detail below by the specific embodiment of the present invention.
Set forth a lot of detail in the following description so that fully understand the present invention, but the present invention can also adopt other to be different from alternate manner described here to implement, those skilled in the art can when without prejudice to doing similar popularization when intension of the present invention, therefore the present invention is by the restriction of following public specific embodiment.
Example 1:
Freshwater catfish oil will be refined melt at 60 DEG C, and keep 30min, then at catfish oil is cooled to 30 DEG C with the rate of temperature fall of 5 DEG C/min, and crystallization 8 hours, the solid fat in catfish oil becomes to analyze.By catfish oil by vacuum filtration, obtain solid fat composition.Point to carry solid fat to contain compared with the catfish higher sn-2 palmitinic acid of oil and total palmitinic acid.Catfish used is oily and divide the lipid acid carrying solid fat form and distribute as shown in the table:
Table 1. catfish is oily and divide the lipid acid composition and distribution of carrying solid fat
The solid fat composition of acidolysis catfish in batch reactor; with 1; 3 specific lipase Lipozyme RMIM are catalyzer; the lipid acid coming from high oleic sunflower oil is adopted to be acry radical donor; catfish oil is 1:6 with the mol ratio of lipid acid; reaction temperature DEG C is 50 DEG C, and enzyme concentration is 10wt%, and stir speed (S.S.) is 500 turns/min.After reaction, by the lipase in centrifugal segregation reaction mixture.
Gained reaction mixture is removed free fatty acids by the mode of molecular distillation, and molecular distillation condition used is: vaporization temperature, 185 DEG C; Heat exchanger temperature, 60 DEG C; Rotating speed, 120rpm; Absolute pressure, 2Pa.The lipid acid of products obtained therefrom forms and distributes as shown in the table:
The lipid acid composition of table 2. enzymolysis product and distribution
| FA kind | FA | sn-2FA | ％sn-2FA | sn-1,3FA |
| C14:0 | 3.59 | 4.10 | 38.07 | 3.34 |
| C16:0 | 22.39 | 57.80 | 86.05 | 4.69 |
| C18:0 | 5.62 | 5.30 | 31.44 | 5.78 |
| C18:1 | 60.10 | 21.88 | 12.14 | 79.21 |
| C18:2 | 7.03 | 8.40 | 39.83 | 6.35 |
| C18:3 | 0.30 | 0.40 | 44.44 | 0.25 |
The triglyceride level of products therefrom and fish oil and solid fat fraction leach-s/tive thereof form contrast as shown in table 3.
The triglyceride level composition of table 3. enzymolysis product
Example 2:
To refine freshwater catfish oil to melt at 50 DEG C, and keep 60min, then catfish oil is down to 20 DEG C with the rate of temperature fall of 3 DEG C/min, crystallization 7 hours, in catfish oil, solid fat becomes to analyze.By the vacuum filtration of catfish oil, obtain solid fat composition.Point to carry solid fat to contain compared with the catfish higher sn-2 palmitinic acid of oil and total palmitinic acid.Gained catfish oil content is carried the lipid acid composition of solid fat and is distributed as shown in table 4 below:
Table 4.20 DEG C catfish oil content proposes lipid acid composition and the distribution of solid fat
The solid fat composition of acidolysis catfish in packed bed flow reactor; with 1; 3 specific lipase Lipozyme TL IM are catalyzer; the lipid acid coming from high gas oil ratio rapeseed oil is adopted to be acry radical donor; catfish oil is 1:5 with the mol ratio of lipid acid; temperature of reaction is 40 DEG C, and the substrate residence time is 2 hours.After reaction, by mechanical impurity presumable in centrifugal segregation reaction mixture.
Gained reaction mixture is removed free fatty acids by the mode of molecular distillation, and molecular distillation condition used is: vaporization temperature, 180 DEG C; Heat exchanger temperature, 60 DEG C; Rotating speed, 130rpm; Absolute pressure, 3Pa.The lipid acid of products obtained therefrom forms and distributes as shown in table 5 below:
The lipid acid composition of table 5. enzymolysis product and distribution
| FA kind | FA | sn-2FA | ％sn-2FA | sn-1,3FA |
| C14:0 | 3.42 | 4.15 | 40.45 | 3.06 |
| C16:0 | 23.39 | 57.10 | 81.37 | 6.54 |
| C18:0 | 5.67 | 5.51 | 32.39 | 5.75 |
| C18:1 | 59.60 | 21.17 | 11.84 | 78.82 |
| C18:2 | 7.22 | 8.86 | 40.90 | 6.40 |
| C18:3 | 0.30 | 0.40 | 44.44 | 0.25 |
The triglyceride level composition of products therefrom is as shown in table 6:
The triglyceride level composition of table 6. enzymolysis product
Example 3:
Freshwater catfish oil will be refined melt at 55 DEG C, and keep 50min, then catfish oil will be cooled to 25 DEG C with the rate of temperature fall of 2 DEG C/min, and crystallization 10 hours, the solid fat in catfish oil becomes to analyze.By catfish oil by vacuum filtration, obtain solid fat composition.Point to carry solid fat to contain compared with the catfish higher sn-2 palmitinic acid of oil and total palmitinic acid.Gained catfish oil content is carried the lipid acid composition of solid fat and is distributed as shown in table 7 below:
Table 7.25 DEG C catfish oil content proposes lipid acid composition and the distribution of solid fat
| FA kind | FA | sn-2FA | ％sn-2FA | sn-1,3FA |
| C12:0 | 0.33 | 0.59 | 59.60 | 0.20 |
| C14:0 | 4.72 | 4.38 | 30.93 | 4.89 |
| C16:0 | 34.88 | 58.89 | 56.28 | 22.88 |
| C16:1 | 0.49 | 0.62 | 42.18 | 0.43 |
| C18:0 | 9.22 | 4.88 | 17.64 | 11.39 |
| C18:1 | 37.57 | 18.93 | 16.80 | 46.89 |
| C18:2 | 8.62 | 8.74 | 33.80 | 8.56 |
| C18:3 | 0.52 | 0.41 | 26.28 | 0.58 |
| C20:0 | 0.51 | 0.39 | 25.49 | 0.57 |
| C20:1 | 1.28 | 0.35 | 9.11 | 1.75 |
| C20:2 | 0.23 | 0.12 | 17.39 | 0.29 |
| C20:3 | 0.32 | 0.21 | 21.88 | 0.38 |
| C20:4 | 0.17 | 0.10 | 19.61 | 0.21 |
| C22:0 | 0.35 | 0.15 | 14.29 | 0.45 |
| C22:1 | 0.31 | 0.08 | 8.60 | 0.43 |
| C22:2 | 0.08 | 0.06 | 25.00 | 0.09 |
| C24:1 | 0.11 | 0.05 | 15.15 | 0.14 |
| C22:4 | 0.05 | 0.07 | 46.67 | 0.04 |
| C22:5 | 0.09 | 0.10 | 37.04 | 0.09 |
| C22:6 | 0.08 | 0.08 | 33.33 | 0.08 |
The solid fat composition of acidolysis catfish oil in packed bed flow reactor; with 1; 3 specific lipase Lipozyme TL IM are catalyzer; the lipid acid coming from high gas oil ratio rapeseed oil is adopted to be acry radical donor; catfish oil is 1:4 with the mol ratio of lipid acid; temperature of reaction is 60 DEG C, and the substrate residence time is 0.5 hour.After reaction, by mechanical impurity presumable in centrifugal segregation reaction mixture.
Gained reaction mixture is removed free fatty acids by the mode of molecular distillation, and molecular distillation condition used is: vaporization temperature, 185 DEG C; Heat exchanger temperature, 60 DEG C; Rotating speed, 120rpm; Absolute pressure, 2Pa.The lipid acid of products obtained therefrom forms and distributes as shown in table 8 below:
The lipid acid composition of table 8. enzymolysis product and distribution
| FA kind | FA | sn-2FA | ％sn-2FA | sn-1,3FA |
| C14:0 | 3.48 | 4.01 | 38.41 | 3.22 |
| C16:0 | 24.49 | 57.3 | 77.99 | 8.09 |
| C18:0 | 5.43 | 5.62 | 34.50 | 5.34 |
| C18:1 | 58.33 | 21.07 | 12.04 | 76.96 |
| C18:2 | 7.42 | 9.02 | 40.52 | 6.62 |
| C18:3 | 0.2 | 0.4 | 66.67 | 0.10 |
The triglyceride level composition of products therefrom is as shown in table 9:
The triglyceride level composition of table 9. enzymolysis product
Thus, find by analyzing, the total palmitic acid content of catfish oil is about 30%, and the palmitinic acid of nearly more than 40%, in sn-2 position, is the very good material of preparation OPO.According to lipid acid composition and the distribution of catfish oil, put forward by dividing the part being rich in sn-2 palmitinic acid in enrichment catfish oil, then with sn-1; 3 selected fat enzymes are catalyzer; with the lipid acid of high gas oil ratio vegetable oil source for acry radical donor, acidolysis divides carries catfish oil, can obtain the product of high OPO content.
The present invention is oily for raw material with catfish first; 1 is rich in conjunction with point mentioning that enzyme process acidolysis prepares; 3-bis-oleic acid-2-palmitic acid three ester product; by dividing the triglyceride level composition carried containing sn-2 palmitinic acid in enrichment catfish oil; again with the free fatty acids of high gas oil ratio vegetable oil source for acry radical donor; obtain being rich in OPO product by acidolysis.The present invention is raw materials used cheap, and products obtained therefrom OPO content is high, can be used as additive and is widely used in baby formula milk powder fat.
It should be noted that, above embodiment is only in order to illustrate technical scheme of the present invention and unrestricted, although with reference to preferred embodiment to invention has been detailed description, those of ordinary skill in the art is to be understood that, can modify to technical scheme of the present invention or equivalent replacement, and not departing from the spirit and scope of technical solution of the present invention, it all should be encompassed in the middle of right of the present invention.
Claims (9)
1. prepare a method for OPO, it is characterized in that: comprise,
By catfish oil 50 ~ 60 DEG C of fusings, keep 30 ~ 60min, and be cooled to 15 ~ 30 DEG C with the rate of temperature fall of 1 ~ 5 DEG C/min, after catfish oil is kept 5 ~ 48h at this temperature, adopt the mode of filtering to remove liquid oil, obtain the solid fat composition of catfish oil being rich in palmitinic acid in sn-2 position;
With sn-1,3 specific lipases are catalyzer, and with the free fatty acids of high gas oil ratio vegetable oil source for acry radical donor, described in acidolysis, the solid fat composition of catfish oil, obtains the product being rich in OPO after removing free fatty acids.
2. the method preparing OPO according to claim 1, is characterized in that: described catalyzer is Lipozyme RM IM and/or Lipozyme TL IM.
3. the method preparing OPO according to claim 1, is characterized in that: described high gas oil ratio vegetables oil is one or more in high gas oil ratio rapeseed oil, high oleic sunflower oil and sweet oil.
4. the method preparing OPO according to claim 1, is characterized in that: described acidolysis, and its temperature of reaction is 40 DEG C ~ 70 DEG C.
5. the method preparing OPO according to claim 1, is characterized in that: described catfish oil is 1:1 ~ 10 with the mol ratio of free fatty acids.
6. the preparation 1 according to claim 1,4 or 5, the method of 3-bis-oleic acid-2-palmitic acid three ester, it is characterized in that: described acidolysis is rhythmic reaction, its enzyme concentration is 3% ~ 15wt%, reaction times is 1h ~ 5h, and stir speed (S.S.) is 300r/min ~ 800r/min.
7. the method preparing OPO according to claim 1,4 or 5, is characterized in that: described acidolysis is successive reaction, and its substrate residence time is at 0.5h ~ 3h.
8. the method preparing OPO according to claim 1, is characterized in that: described removing free fatty acids is centrifugation or filtration.
9. the method preparing OPO according to claim 1, is characterized in that: described removing free fatty acids is molecular distillation or underpressure distillation.
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| PCT/CN2015/096269 WO2016176987A1 (en) | 2015-05-06 | 2015-12-03 | Preparation method for structured lipid rich in 1,3-dioleate-2-palmitic acid triglyceride |
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| WO2016176987A1 (en) * | 2015-05-06 | 2016-11-10 | 江南大学 | Preparation method for structured lipid rich in 1,3-dioleate-2-palmitic acid triglyceride |
| CN111317068A (en) * | 2020-01-15 | 2020-06-23 | 广州市优百特饲料科技有限公司 | Feeding OPO breast milk structure fat and preparation method and application thereof |
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